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Vacation Homes in Osceola

Osceola
Wed, 18 Nov 2026 - Thu, 19 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 2.000+ Vacation Homes in Osceola
Interior

Fp8208 Windsor Palms Resort Vacation Home

Vacation Home

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Osceola
Fp8208 Windsor Palms Resort Vacation Home Location
With a stay at this cottage in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and Old Town. This cottage is 7.1 mi (11.4 km) from ESPN Wide World of Sports Complex and 7.5 mi (12.1 km) from Disney's Hollywood Studios®.

Fp8208 Windsor Palms Resort Vacation Home Rooms
Make yourself comfortable in this air-conditioned cottage, which has a kitchen. Cable television is provided for your entertainment. Conveniences include a dryer and an iron/ironing board.

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Dog-friendly Getaway With Private Pool + Spa, Putting Green, Patio, & Game Room

Vacation Home

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Osceola
Dog-friendly Getaway With Private Pool + Spa, Putting Green, Patio, & Game Room Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 10-minute drive of Mystic Dunes Golf Club and ChampionsGate Golf Club. This vacation home is 5.4 mi (8.8 km) from Walt Disney World® Resort and 7.7 mi (12.4 km) from ESPN Wide World of Sports Complex.

Dog-friendly Getaway With Private Pool + Spa, Putting Green, Patio, & Game Room Facility and Service
Take advantage of recreation opportunities such as an outdoor pool, or other amenities including complimentary wireless internet access and an arcade/game room.

Dog-friendly Getaway With Private Pool + Spa, Putting Green, Patio, & Game Room Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Dazzling Home With Putting Green at Encore

Vacation Home

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Osceola
Dazzling Home With Putting Green at Encore Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 10-minute drive of Mystic Dunes Golf Club and Reunion Resort Golf Course. This family-friendly vacation home is 5.4 mi (8.7 km) from Walt Disney World® Resort and 7.7 mi (12.3 km) from ESPN Wide World of Sports Complex.

Dazzling Home With Putting Green at Encore Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Dazzling Home With Putting Green at Encore Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Room

Family Home 9 BR 8 Min to Disney!

Vacation Home

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Osceola
Family Home 9 BR 8 Min to Disney! Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 6.2 mi (9.9 km) from Disney Springs™ and 7.1 mi (11.5 km) from ESPN Wide World of Sports Complex.

Family Home 9 BR 8 Min to Disney! Facility and Service
Take advantage of recreation opportunities such as an outdoor pool, or other amenities including complimentary wireless internet access and an arcade/game room.

Family Home 9 BR 8 Min to Disney! Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Exterior & Views

Shd4720

Vacation Home

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Osceola
Shd4720 Location
With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This cottage is 6 mi (9.6 km) from Disney Springs™ and 6.6 mi (10.7 km) from Walt Disney World® Resort.

Shd4720 Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with an oven and a stovetop. Conveniences include a desk and a microwave.

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Bedroom

4 Bed 2245

Private Vacation Home

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Osceola
4 Bed 2245 Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Walt Disney World® Resort and Old Town. This vacation home is 8.2 mi (13.2 km) from Disney's Hollywood Studios® and 9.2 mi (14.9 km) from Disney's Animal Kingdom® Theme Park.

4 Bed 2245 Facility and Service
Enjoy recreation amenities such as an outdoor pool or take in the view from a terrace.

4 Bed 2245 Rooms
Your vacation home features a flat-screen TV. Complimentary wireless internet access is available to keep you connected.

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1.0/5
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Others

Oakwater by PRP

Vacation Home

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Osceola
Oakwater by PRP Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Old Town. This vacation home is 5 mi (8 km) from ESPN Wide World of Sports Complex and 5.5 mi (8.8 km) from Disney's Hollywood Studios®.

Oakwater by PRP Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including an arcade/game room.

Oakwater by PRP Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private hot tub. There's a private balcony. A kitchen is outfitted with a refrigerator, a microwave, and a dishwasher. Satellite programming and a DVD player are provided for your entertainment, while complimentary wireless internet access keeps you connected.

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Others

Champions Gate Near Disney Privacy In Back! 6 Bedroom Home by RedAwning

Vacation Home

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Osceola
Champions Gate Near Disney Privacy In Back! 6 Bedroom Home by RedAwning Location
With a stay at this vacation home in Four Corners (Champions Gate), you'll be within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This vacation home is 11.7 mi (18.9 km) from Old Town and 12.5 mi (20.1 km) from ESPN Wide World of Sports Complex.

Champions Gate Near Disney Privacy In Back! 6 Bedroom Home by RedAwning Facility and Service
This smoke-free vacation home offers a foosball table.

Champions Gate Near Disney Privacy In Back! 6 Bedroom Home by RedAwning Rooms
Make yourself comfortable in this vacation home, which has a kitchen. Complimentary wireless internet access keeps you connected, and a DVD player is provided for your entertainment.

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Welcome to The Dream Getaway

Vacation Home

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Osceola
Welcome to The Dream Getaway Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be within a 15-minute drive of Reunion Resort Golf Course and ChampionsGate Golf Club. This vacation home is 7.7 mi (12.4 km) from Walt Disney World® Resort and 10 mi (16 km) from ESPN Wide World of Sports Complex.

Welcome to The Dream Getaway Facility and Service
Take advantage of recreation opportunities such as an outdoor pool, or other amenities including complimentary wireless internet access and an arcade/game room.

Welcome to The Dream Getaway Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Bedroom

19 Guest Home w Pool Hot Tub Cinema BBQ

Vacation Home

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Osceola
19 Guest Home w Pool Hot Tub Cinema BBQ Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This family-friendly vacation home is 9.1 mi (14.6 km) from Disney Springs™ and 10.1 mi (16.2 km) from Walt Disney World® Resort.

19 Guest Home w Pool Hot Tub Cinema BBQ Facility and Service
Make use of convenient amenities such as complimentary wireless internet access, an arcade/game room, and gas grills.

19 Guest Home w Pool Hot Tub Cinema BBQ Rooms
Make yourself comfortable in your air-conditioned vacation home, which features a Smart TV. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment.

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2.5/5
Fully Booked
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The Themepark Palace With Home Theater at Encore

Vacation Home

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Osceola
The Themepark Palace With Home Theater at Encore Location
When you stay at this villa in Kissimmee, you'll be near the beach, within a 10-minute drive of Mystic Dunes Golf Club and Reunion Resort Golf Course. This family-friendly villa is 5.7 mi (9.1 km) from Walt Disney World® Resort and 7.9 mi (12.7 km) from ESPN Wide World of Sports Complex.

The Themepark Palace With Home Theater at Encore Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

The Themepark Palace With Home Theater at Encore Rooms
Make yourself comfortable in your individually decorated villa. The bathroom has a bathtub or shower.

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Others

Dainty Home With Themed Bedrooms at Encore

Vacation Home

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Osceola
Dainty Home With Themed Bedrooms at Encore Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 10-minute drive of Mystic Dunes Golf Club and Reunion Resort Golf Course. This vacation home is 5.5 mi (8.8 km) from Walt Disney World® Resort and 7.7 mi (12.4 km) from ESPN Wide World of Sports Complex.

Dainty Home With Themed Bedrooms at Encore Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including an arcade/game room.

Dainty Home With Themed Bedrooms at Encore Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Others

Grhmll1505 - Champions Gate Resort - 6 Bed 6 Baths House

Vacation Home

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Osceola
Grhmll1505 - Champions Gate Resort - 6 Bed 6 Baths House Location
With a stay at this vacation home in Four Corners (Champions Gate), you'll be within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This family-friendly vacation home is 11.3 mi (18.1 km) from Old Town and 12 mi (19.4 km) from ESPN Wide World of Sports Complex.

Grhmll1505 - Champions Gate Resort - 6 Bed 6 Baths House Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools or 2 hot tubs. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhmll1505 - Champions Gate Resort - 6 Bed 6 Baths House Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private plunge pool and a private hot tub. There's a private balcony or patio. A kitchen is outfitted with a refrigerator, an oven, and a microwave. A flat-screen television is provided for your entertainment.

Restaurant and Cafe
Enjoy a meal at the restaurant or snacks in the vacation home's coffee shop/cafe. Unwind at the end of the day with a drink at the bar/lounge or the poolside bar.

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Exterior & Views

Fd57055 - Lucaya Village - 4 Bed 3 Baths Townhouse

Vacation Home

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Osceola
Fd57055 - Lucaya Village - 4 Bed 3 Baths Townhouse Location
With a stay at this vacation home in Kissimmee, you'll be a 3-minute drive from Old Town and 7 minutes from Orlando Vineland Premium Outlets. This golf vacation home is 5.2 mi (8.4 km) from Disney Springs™ and 5.6 mi (9 km) from Walt Disney World® Resort.

Fd57055 - Lucaya Village - 4 Bed 3 Baths Townhouse Facility and Service
Practice your swing on the golf course or dip into one of the 2 hot tubs. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Fd57055 - Lucaya Village - 4 Bed 3 Baths Townhouse Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. There's a private balcony. A flat-screen television is provided for your entertainment. Conveniences include a microwave and a sofa bed.

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Others

1516mb- the Retreat at Championsgate

Vacation Home

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Osceola
1516mb- the Retreat at Championsgate Location
With a stay at this vacation home in Four Corners (Champions Gate), you'll be within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This golf vacation home is 11.3 mi (18.2 km) from Old Town and 12.1 mi (19.4 km) from ESPN Wide World of Sports Complex.

1516mb- the Retreat at Championsgate Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

1516mb- the Retreat at Championsgate Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and a stovetop. A flat-screen television is provided for your entertainment. Conveniences include a microwave and an iron/ironing board.

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Room

Limited-time Special Discounts Spacious Home w/ Pool and Resort Amenities

Vacation Home

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Osceola
Limited-time Special Discounts Spacious Home w/ Pool and Resort Amenities Location
When you stay at Limited-time Special Discounts Spacious Home w/ Pool and Resort Amenities in Kissimmee, you'll be near the beach, within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club.

Limited-time Special Discounts Spacious Home w/ Pool and Resort Amenities Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

Limited-time Special Discounts Spacious Home w/ Pool and Resort Amenities Rooms
The bathroom has a bathtub or shower.

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2767lkd-emerald Island Resort 7 Bedroom Home

Vacation Home

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Osceola
2767lkd-emerald Island Resort 7 Bedroom Home Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Walt Disney World® Resort and Old Town. This vacation home is 7.2 mi (11.7 km) from ESPN Wide World of Sports Complex and 7.7 mi (12.4 km) from Disney's Hollywood Studios®.

2767lkd-emerald Island Resort 7 Bedroom Home Rooms
Make yourself comfortable in your vacation home, featuring a refrigerator and a Smart TV. Complimentary wireless internet access is available to keep you connected. The bathroom has a bathtub or shower.Conveniences include a coffee/tea maker and a washing machine.

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Bathroom

Gorgeous 4 Bd Close to Disney @ Magic Village 3114

Vacation Home

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Osceola
Gorgeous 4 Bd Close to Disney @ Magic Village 3114 Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Old Town. This luxury vacation home is 5.3 mi (8.5 km) from ESPN Wide World of Sports Complex and 5.8 mi (9.3 km) from Disney's Hollywood Studios®.

Gorgeous 4 Bd Close to Disney @ Magic Village 3114 Facility and Service
Take in the views from a garden and make use of amenities such as concierge services and a television in a common area. Additional amenities at this vacation home include charcoal grills and a vending machine.

Gorgeous 4 Bd Close to Disney @ Magic Village 3114 Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a full-sized refrigerator/freezer and an oven. A 60-inch Smart television with cable programming provides entertainment, while complimentary wired internet access keeps you connected. Conveniences include a safe and a desk, and you can also request a crib/infant bed (surcharge).

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4.8/5
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Room

Beautiful Home With Private Pool, Screened Lanai, Wifi, Private W/d, and AC

Vacation Home

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Osceola
Beautiful Home With Private Pool, Screened Lanai, Wifi, Private W/d, and AC Location
With a stay at this vacation home in Kissimmee (Lake Berkley), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 9 mi (14.5 km) from Disney Springs™ and 9.2 mi (14.8 km) from Walt Disney World® Resort.

Beautiful Home With Private Pool, Screened Lanai, Wifi, Private W/d, and AC Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Beautiful Home With Private Pool, Screened Lanai, Wifi, Private W/d, and AC Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

See details
Fully Booked
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Exterior & Views

Ov3835 - Champions Gate Resort - 5 Bed 4 Baths Townhome

Vacation Home

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Osceola
Ov3835 - Champions Gate Resort - 5 Bed 4 Baths Townhome Location
With a stay at this vacation home in Four Corners (Champions Gate), you'll be within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This family-friendly vacation home is 11.7 mi (18.9 km) from Old Town and 12.5 mi (20.1 km) from ESPN Wide World of Sports Complex.

Ov3835 - Champions Gate Resort - 5 Bed 4 Baths Townhome Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools or 2 hot tubs. Additional features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Ov3835 - Champions Gate Resort - 5 Bed 4 Baths Townhome Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private plunge pool and a private hot tub. There's a private balcony or patio. A kitchen is outfitted with a refrigerator, an oven, and a microwave. A flat-screen television is provided for your entertainment.

Restaurant and Cafe
Enjoy a meal at the restaurant or snacks in the vacation home's coffee shop/cafe. Relax with your favorite drink at the bar/lounge or the poolside bar.

See details
Fully Booked
Let's check on other dates!
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Vacation Homes in Osceola

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